1-Chloro-3,6-dioxaoct-8-yl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside | 126765-23-9

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 1-Chloro-3,6-dioxaoct-8-yl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside
• 英文别名: 2-[2-(2-chloroethoxy)ethoxy]ethyl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside；1-Chloro-3,6-dioxaoct-8-yl 2,3,4,6-tetra-O-acetyl-beta-D-galactopyranoside；[(2R,3S,4S,5R,6R)-3,4,5-triacetyloxy-6-[2-[2-(2-chloroethoxy)ethoxy]ethoxy]oxan-2-yl]methyl acetate
• CAS: 126765-23-9
• 化学式: C₂₀H₃₁ClO₁₂
• 分子量: 498.912
• InChiKey: JOOZTROIEWMDGM-LCWAXJCOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.9
• 重原子数：
  33
• 可旋转键数：
  18
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  142
• 氢给体数：
  0
• 氢受体数：
  12

反应信息

• 作为反应物：
  描述：

  1-Chloro-3,6-dioxaoct-8-yl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside 在 吡啶 、 4-二甲氨基吡啶 、 ammonium cerium(IV) nitrate 、 二正丁基氧化锡 、 sodium carbonate 作用下， 以 甲醇 、 水 、 乙腈 为溶剂， 反应 51.0h， 生成 1-chloro-3,6-dioxa-8-octyl 2,4,6-tri-O-acetyl-β-D-galactoside
  参考文献：
  名称：

  Frontal Affinity Chromatography Coupled to Mass Spectrometry: An Effective Method for K_dDetermination and Screening of α‐Gal Derivatives Binding to Anti‐Gal Antibodies (IgG)

  摘要：

  Frontal affinity chromatography with mass spectrometric detection (FAC/MS) was developed as an effective method for rapid determination of K-d values for alpha-Gal derivatives binding to human anti-Gal IgG antibodies. Using this method, K-d values for 23 alpha-Gal compounds were determined for the first time, including an alpha-Gal terminated N-linked oligosaccharide which mimics a single N-glycoform present on the surface of animal cells. A mixture of eight alpha-Gal derivatives, a model for an alpha-Gal compound library, was successfully screened against this anti-Gal IgG using FAC/MS. The analyte breakthrough sequence, indicated by the ion chromatogram, reflected the magnitude of the K-d values, confirming its potential application in the screening of new alpha-Gal derivatives and mimetics. Ten alpha-Gal derivatives were designed and synthesized chemically or enzymatically. Among the compounds analyzed, trivalent compound 26 demonstrated the strongest binding affinity to anti-Gal IgG with a K-d value of 3.1 muM. The alpha-Gal terminated N-linked oligosaccharide 28 had a K-d value of 8.6 muM.

  DOI：

  10.1081/car-120025323
• 作为产物：
  描述：

  1,2,3,4,6-戊-O-乙酰-a-D-吡喃半乳糖 在 三氟甲磺酸三甲基硅酯 、 乙酸肼 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 二氯甲烷 、 N,N-二甲基甲酰胺 为溶剂， 反应 2.0h， 生成 1-Chloro-3,6-dioxaoct-8-yl 2,3,4,6-tetra-O-acetyl-β-D-galactopyranoside
  参考文献：
  名称：

  寡糖-喜树碱偶联物作为潜在的抗肿瘤药：设计，合成和生物学评估。

  摘要：

  合成了三十种新颖的20（S）-O-连接的喜树碱（CPT）糖缀合物。他们表现出更有效的体外细胞毒性过伊立替康，但非常弱的直接拓扑异构酶I在100.0观察（TOPO I）抑制μ M.寡糖类型，PEG接头的长度和乙酰基作用于细胞毒性，选择性，水溶性明显影响，并新合成的CPT糖缀合物的稳定性。结构40与CPT相比，博来霉素（BLM）二糖与引入的酯部分中的二甘醇相连，具有更高的抗肿瘤活性和独特的选择性。静脉内动物急性毒性（160 mg / kg）未检测到毒性。总的来说，将具有靶向肿瘤的寡糖附着到CPT的20（S）-OH上可以为当前的Topo I毒药带来的艰巨问题提供解决方案。

  DOI：

  10.1016/j.ejmech.2020.112509

文献信息

• Multivalent recognition of lectins by glyconanoparticle systems
  作者：Eugene Mahon、Teodor Aastrup、Mihail Barboiu

  DOI：10.1039/c002652b

  日期：——

  Multivalent recognition of lectin layers by glyconanoparticle sugar-clusters has been used to study the carbohydrate–protein interactions in a QCM sensing setup.

  多价凝集素层通过糖纳米颗粒糖簇的识别已被用于在QCM传感系统中研究碳水化合物-蛋白质相互作用。
• METHOD FOR THE SYNTHESIS OF OLIGONUCLEOTIDE DERIVATIVES
  申请人：Morvan Francois

  公开号：US20090124571A1

  公开（公告）日：2009-05-14

  Method for the synthesis of nucleotide derivatives wherein molecules of interest are grafted on the oligonucleotide with the help of a “click chemistry” reaction between an azide function on the molecule of interest and an alkyne function on the oligonucleotide, or between an alkyne function on the molecule of interest and an azide function on the oligonucleotide. Intermediate molecules, notably alkyne functionalized oligonucleotides, grafted oligonucleotides, azide functionalized oligonucleotides, oligonucleotide micro arrays containing them and the use of those grafted oligonucleotides for biological investigation and for cell targeting.

  核苷酸衍生物合成方法，其中感兴趣的分子通过“点击化学”反应被嫁接到寡核苷酸上，该反应在感兴趣分子上的偶氮功能与寡核苷酸上的炔基功能之间，或者在感兴趣分子上的炔基功能与寡核苷酸上的偶氮功能之间进行。中间分子，特别是炔基功能化的寡核苷酸，嫁接的寡核苷酸，偶氮功能化的寡核苷酸，包含它们的寡核苷酸微阵列以及利用这些嫁接的寡核苷酸进行生物研究和细胞靶向的用途。
• CuAAC synthesis of resorcin[4]arene-based glycoclusters as multivalent ligands of lectins
  作者：Zahid H. Soomro、Samy Cecioni、Helen Blanchard、Jean-Pierre Praly、Anne Imberty、Sébastien Vidal、Susan E. Matthews

  DOI：10.1039/c1ob05676j

  日期：——

  azide–alkyne click chemistry is described. ELLA binding studies confirm that galactose sugar clusters are effective ligands for the PA-IL bacterial lectin of Pseudomonas aeruginosa while poor binding for the lactose-based monovalent probe and no binding could be measured for the multivalent glycoclusters was observed for the human galectin-1.

  合成的多价糖簇显示出有望用作治疗细菌感染的抗粘剂。在这里我们报告一个四价家族的合成半乳糖和基于间苯二酚[4]芳烃核心的乳糖官能化大环化合物。描述了通过铜催化的叠氮化物-炔键点击化学形成低边缘炔丙基间苯二酚[4]芳烃的非对映选择性合成途径的发展。ELLA结合研究证实半乳糖糖簇是铜绿假单胞菌PA-IL细菌凝集素的有效配体，而基于乳糖的单价探针的结合较弱，而人半乳糖凝集素-1的多价糖簇未见结合。
• Site-selective modification of proteins for the synthesis of structurally defined multivalent scaffolds
  作者：Lukas M. Artner、Lars Merkel、Nina Bohlke、Figen Beceren-Braun、Christoph Weise、Jens Dernedde、Nediljko Budisa、Christian P. R. Hackenberger

  DOI：10.1039/c1cc16039g

  日期：——

  A combination of classical site-directed mutagenesis, genetic code engineering and bioorthogonal reactions delivered a chemically modified barstar protein with one or four carbohydrates installed at specific residues. These protein conjugates were employed in multivalent binding studies, which support the use of proteins as structurally defined scaffolds for the presentation of multivalent ligands.

  经典的定点突变、遗传密码工程和生物正交反应相结合，产生了在特定残基上安装了一种或四种碳水化合物的化学修饰巴氏星蛋白质。这些蛋白质共轭物被用于多价配体结合研究，支持将蛋白质作为结构明确的支架来呈现多价配体。
• <b>Synthesis of Dodecavalent Fullerene‐Based Glycoclusters and Evaluation of Their Binding Properties towards a Bacterial Lectin</b>
  作者：Samy Cecioni、Vincent Oerthel、Julien Iehl、Michel Holler、David Goyard、Jean‐Pierre Praly、Anne Imberty、Jean‐François Nierengarten、Sébastien Vidal

  DOI：10.1002/chem.201003258

  日期：2011.3.7

  biological processes and particularly in lectin–carbohydrate interactions. The design of high‐affinity ligands of lectins should provide molecules capable of interfering with these biological processes and potentially inhibit bacterial or viral infections. Azide–alkyne “click” chemistry was applied to the synthesis of dodecavalent fullerene‐based glycoclusters. The conjugation could be efficiently performed

  多价在生物过程中，尤其是在凝集素与碳水化合物的相互作用中起着重要作用。凝集素的高亲和力配体的设计应提供能够干扰这些生物学过程并可能抑制细菌或病毒感染的分子。叠氮化物-炔烃“点击”化学方法被用于合成基于十二价富勒烯的糖团。结合可以有效地通过任何一个配偶体上的炔或叠氮化物功能（即六-富勒烯加合物或糖苷）来完成。PA‐IL是一种来自机会性病原菌铜绿假单胞菌的细菌凝集素并参与人体组织糖缀合物的识别。获得的糖簇被评估为PA‐IL的配体，并评估了其与糖基化表面竞争的潜力。通过血凝抑制测定法（HIA），酶联凝集素测定法（ELLA）和表面等离振子共振（SPR）测得的亲和力显示出显着的“糖苷簇效应”，与单价比较时结合力最多可增加12000倍碳水化合物参考探针，具有基于十二价富勒烯的糖簇，尽管根据分析技术有所不同。